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682373 Sigma-Aldrich

Hoveyda-Grubbs Catalyst® M721

Umicore

Synonym: Dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](2-isopropoxyphenylmethylene)ruthenium(II), Hoveyda-Grubbs Catalyst® M72 SI(o-Tol) (C571), Stewart-Grubbs catalyst

  • CAS Number 927429-61-6

  • Empirical Formula (Hill Notation) C27H30Cl2N2ORu

  • Molecular Weight 570.52

  •  MDL number MFCD09265166

  •  PubChem Substance ID 24885712

  •  NACRES NA.22

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Properties

Related Categories Catalysis and Inorganic Chemistry, Catalysts for Polymerization, Chemical Synthesis, Grubbs Catalyst Technology for Olefin Metathesis by Sigma-Aldrich, Materials Science,
Quality Level   100
mp   199-208 °C
reaction suitability   reagent type: catalyst
reaction type: Ring-Opening Polymerization
storage temp.   2-8°C
SMILES string   CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3ccccc3C)c4ccccc4C
InChI   1S/C17H18N2.C10H12O.2ClH.Ru/c1-14-7-3-5-9-16(14)18-11-12-19(13-18)17-10-6-4-8-15(17)2;1-8(2)11-10-7-5-4-6-9(10)3;;;/h3-10H,11-12H2,1-2H3;3-8H,1-2H3;2*1H;/q;;;;+2/p-2
InChI key   ZDJCARGGZRTYFH-UHFFFAOYSA-L

Description

Application

Less sterically hindered analog of Hoveyda-Grubbs Catalyst® 2nd Generation. Excels at ring-closing metathesis reactions of sterically encumbered olefins. Also useful for the cross metathesis of olefins bearing large allylic substituents.

Packaging

100, 500 mg in glass bottle

2 g in glass bottle

Other Notes

Grubbs Catalyst® Technology for Olefin Metathesis by Aldrich

Legal Information

Product of Umicore

Product License
This product, its manufacturing or use, is the subject of one or more issued or pending U.S. Patents (and foreign equivalents) owned or controlled by Umicore PMC. The purchase of this product from Umicore PMC through Sigma-Aldrich, its affiliates or their authorized distributors conveys to the buyer a limited, one-time, non-exclusive, non-transferable, non-assignable license. Buyer’s use of this product may infringe patents owned or controlled by third parties. It is the sole responsibility of buyer to ensure that its use of the product does not infringe the patent rights of third parties or exceed the scope of the license granted herein.

For any further information on product please refer to your local Umicore PMC contact at http://www.pmc.umicore.com

Grubbs Catalyst is a registered trademark of Umicore

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Cross Metathesis Reaction of Hindered Substrates

Exploiting the ability of the o-tolyl-NHC Hoveyda-Grubbs catalyst to react with hindered substrates, the Grubbs group recently reported a series of cross metathesis reactions between terminal olefins...
William Sommer
Aldrich ChemFiles 2009, 9.6, 7.
Keywords: Chemfiles, Cross metathesis, Ligands, Metathesis, Reductions

Grubbs Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Grubbs Group - Professor Product Portal
Keywords: Catalysis, Cross metathesis, Dihydroxylations, Ligands, Metathesis, Nuclear magnetic resonance spectroscopy, Olefin metathesis, Pharmaceutical, Spectroscopy, transformation

Ring Closing Metathesis Reaction Screening Kit Materials

The screening sets come pre-loaded with 1 µmol of catalyst in each vial according to the following design.
Keywords: High performance liquid chromatography, Metathesis, Ring-closing metathesis

Ring-Closing Metathesis | Aldrich ChemFiles 2009, 9.6, 4.

Ring-closing metathesis has become an essential tool for C-C bond formation as demonstrated by the profound impact on total synthesis in recent years.1 The first examples date back to 1980 and involv...
William Sommer
Aldrich ChemFiles 2009, 9.6, 4.
Keywords: C-C bond formation, Cyclizations, Metathesis, Ring-closing metathesis

Sterically Accessible Catalysts for Hindered Substrates

More recently, Stoltz and Grubbs jointly reported the use of ringclosing metathesis in the key step of the total synthesis of (+)–elatol, a spiro[5.5]undecane-containing natural product which has dra...
William Sommer
Aldrich ChemFiles 2009,9.6, 5.
Keywords: Antifungals, Asymmetric synthesis, Chemfiles, Metathesis

Synthesis of Tetrasubstituted Olefins

In their preparation of sominone (R = OH, 22ß-O) and related analogs, Matsuya and coworkers used RCM to generate tetrasubstituted olefins. The RCM reaction was utilized in the preparation of the lact...
William Sommer
Aldrich ChemFiles 2009,9.6, 5.
Keywords: Chemfiles

Related Content

Metathesis in Chemical Synthesis

Olefin metathesis is now a well-entrenched synthetic technique, and is a powerful method for the clean construction of innumerable classes of chemical architectures. The broadly accepted belief that ...
Keywords: Building blocks, Cross metathesis, Enyne metathesis, Exothermic, Isomerizations, Ligands, Living polymerization, Metathesis, Olefin metathesis, Organic synthesis, Polymerization reactions, Ring opening metathesis polymerisation, Ring-closing metathesis

Peer-Reviewed Papers
15

References

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